Live Account For My Son

Sorry if I was unclear. I bought the DLC and games on demand using my Xbox Live account.

Now if I'm reading your post correctly you said you used his Account to buy the content so there should not be any problem. Am I missing a part of the puzzle

Most Games when purchased can be played by anyone on the console as long as the account that purchased the game is stored on the console(if it's Xbox One you need to set your console as the home console). Now with DLC it's tricky. That is down to the game
developers and to be honest most DLC is gamer tag specific so it can not be shared for example if it's a map pack everyone needs to have purchased the map packs.

Is your issue that your son will be using 2 console ? if yes will it be an Xbox One or 360

So I suppose the answer is Games yes DLC most likely not :-(

As long as your profile is on the console & it's the same console that you used to download the games then yes,he should be able to play them

SAME SITUATION

I created a XBOX LIVE account for my son over a decade ago. I used my work email address when I created the gamertag. Back then Microsoft's services were not lumped under one login (that didn't even exist). When Microsoft deployed their one login system they
merged my son's Xbox Live account into my work Microsoft account.

Now my son is an adult. We need to transfer HIS Xbox Live gamertag to HIS Microsoft account.

This is idiotic.

My son is having the same problem with his Xbox360 live account.